Triethylamine → 4-chloro-N-(1-diazo-2-oxopentan-3-yl)-N-(pent-1-yn-3-yl)benzenesulfonamide

HRID 15727

Reaktionsgleichung

Reaktionsgleichung von HRID 15727
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH:17]([CH2:21][CH3:22])[C:18]([OH:20])=O)[CH:12]([CH2:15][CH3:16])[C:13]#[CH:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[N+:38](=[CH2:40])=[N-:39]>CCOCC.CC(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH:17]([CH2:21][CH3:22])[C:18](=[O:20])[CH:40]=[N+:38]=[N-:39])[CH:12]([CH2:15][CH3:16])[C:13]#[CH:14])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 9550DiazomethaneHCID 62365Isobutyl chloroformateHCID 593423732-(4-chloro-N-(pent-1-yn-3-yl)phenylsulfonamido)-butanoic acid

Produkt 1

HCID 722595874-chloro-N-(1-diazo-2-oxopentan-3-yl)-N-(pent-1-yn-3-yl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

To a solution of the compound 60 (498 mg, 1.45 mmol) in 7.5 mL of Et2O were added sequentially 0.24 mL of triethylamine (1.2 eq), 0.23 mL of isobutyl chloroformate (1.2 eq) at −30° C. After being stirred at −30° C. for 15 min, diazomethane (prepared by mixing MNNG and KOH in diethyl ether) (excess) was added to the above mixture at 0° C. and stirred there for 5 hours. Glacial HOAc (1.5 mL) was added to destroy the excess diazomethane and the solution was extracted with EtOAc. The organic phase was washed with sat NaHCO3, water, brine and dried (MgSO4). LCMS 368.1 (M+1).

Aufarbeitung

  1. stirringstirred there for 5 hours
  2. customto destroy the excess diazomethane
  3. extractionthe solution was extracted with EtOAc
  4. washThe organic phase was washed with sat NaHCO3, water, brine
  5. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-c6a04bb7504c4ce18d8cc8e65ca5dd39
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732609B2

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